Piperidine → tert-butyl N-[4-[3-[2-(11-aminoundecanoylamino)-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 723177Notes

Reaction equation

HRID 723177 reaction equation
N1CCCCC1.C1C2C(COC(=O)[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34](=[O:69])[NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[C:37]=3[C:43]3[CH:48]=[CH:47][CH:46]=[C:45]([S:49]([C:52]4[CH:56]=[C:55]([C:57]([NH:59][C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])=[NH:58])[S:54][C:53]=4[S:67][CH3:68])(=[O:51])=[O:50])[CH:44]=3)C3C(=CC=CC=3)C=2C=CC=1>CN(C=O)C>[C:63]([O:62][C:60](=[O:61])[NH:59][C:57]([C:55]1[S:54][C:53]([S:67][CH3:68])=[C:52]([S:49]([C:45]2[CH:44]=[C:43]([C:37]3[C:38]([CH3:42])=[CH:39][CH:40]=[CH:41][C:36]=3[NH:35][C:34](=[O:69])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][NH2:23])[CH:48]=[CH:47][CH:46]=2)(=[O:51])=[O:50])[CH:56]=1)=[NH:58])([CH3:66])([CH3:65])[CH3:64]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 145857666tert-butyl N-[4-[3-[2-[11-(9H-fluoren-9-ylmethoxycarbonylamino)undecanoylamino]-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857685tert-butyl N-[4-[3-[2-(11-aminoundecanoylamino)-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamateYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 50% piperidine in DMF [1 mL] was added to (10-{3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-2-ylcarbamoyl}-decyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (0.040 g, 0.043 mmol) [example 211, step a] and stirred for 0.5 hours, followed by evaporation. Column chromatography (10% MeOH in dichloromethane) of the residue yielded the title compound (0.024 g, 77%) as a solid. ESI-MS (m/z): Calcd. for C35H48N4O5S3: 700.28; found: 701.0.

Workup

  1. customfollowed by evaporation

Sources & evidence

ORD record
ord-ca43dc48005b412b91e5651cd772fea3
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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